


I'm Not Gonna Let You Die a Virgin

by greeneyedsourwolf



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bisexual Dean Winchester, Bottom Dean, Episode Related, Gay Castiel (Supernatural), M/M, Plot What Plot/Porn Without Plot, Smut, Top Castiel, Top Castiel/Bottom Dean Winchester, Virgin Castiel, okay theres some plot
Language: English
Status: Completed
Published: 2018-04-19
Updated: 2018-04-19
Packaged: 2019-04-24 23:05:12
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,245
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14365626
Author URL: https://archiveofourown.org/users/greeneyedsourwolf/pseuds/greeneyedsourwolf
Summary: s5ep03 "Free to Be You and Me" - ChangedDean declares one night before their face-off with Raphael that he will not let Castiel die a virgin. The angel explains he doesn't want a woman when Dean offers to buy him a girl, but then Dean gets another idea...





	I'm Not Gonna Let You Die a Virgin

**Author's Note:**

> Just another fic I expected to be 2,000 words that ended up being 4,300 and had me staying up half the night writing it because I just couldn't stop. Yay, fanfic writing...

“So odds are you’re a dead man tomorrow?” Dean asked.

 

“Yes,” Cas deadpanned with a blank look on his face. 

 

Dean’s eyebrows shot up, and his mouth opened a little in shock. Whatever emotions he was feeling about Cas, his best friend (though he would never admit it), most-likely dying tomorrow he hid quickly, shrugging it off with a small, “Oh.” He grabbed his coat and walked past Cas. He changed the subject, “Well, last night on earth. What, uh… What are your plans?”

 

Cas looked at him with an almost confused look, and then to the floor, “I just thought I’d sit here quietly.”

 

Cas’ lack of personality sometimes surprised Dean, he wondered what the angel had been doing for the last century or two. He had met angels that talked like normal people, like Gabriel for instance. He gave Cas a questioning look, “Dude. Come on. Anything? Hmm? Booze, women?”

 

Cas gave him a very vulnerable, very  _ serious _ look, and then his eyes darted back at the grimy wall in front of him. Dean stood behind him, taking a couple steps forward, “You have been with a woman before, right? Or an angel at least?”

 

Cas rubbed the back of his neck awkwardly, feeling a weight of Dean’s eyes on him. Dean leaned down with an expectant look, “You mean to tell me you’ve never been up there doing a little cloud-seeding?”

 

“Look, I’ve never had occasion, okay?” Cas said with a stern voice. 

 

Dean backed away, an amused look on his face. He nodded with confidence, “All right.” He walked in front of Cas in determination, and threw on his coat, “Let me tell you something, there are two things I know for certain. One, Bert and Ernie are gay. Two, you are not gonna die a virgin. Not on  _ my _ watch.” He closed the book on the table, and walked away, “Let’s go.”

 

\-------

 

“Cas looked positively terrified inside the club, eyes wide and posture straight as he and Dean sat in a black, satiny booth in the middle of the room.

 

“Hey,” Dean caught Castiel’s attention and took a swig of his beer. “Relax,” he said, leaning forward. Cas looked like he was about to have a stroke.

 

“Dean, I’m not sure this is a proper establishment for someone like myself,” Cas practically whispered. An awkward look was plastered on his face, and he knew Dean didn’t understand what he meant. “Not only is this a den of iniquity, but it is…”

 

“What?” Dean asked, he took another sip of his beer. He took a look around at the girls, all dressed in revealing, satiny underwear. “Look, Cas, you rebelled against heaven, you’re allowed to do whatever the fuck you want now. You can  _ fuck _ whoever you want now. Pick one,” he slapped a stack of cash on the table, “You’re hot Cas, you’ll have no problem.”

 

Cas blushed at the comment but shook his head. “Dean you don’t understand… I don’t… I don’t think I would enjoy this,” he said, gesturing to the room around them.

 

Dean’s head tilted, his eyes scrunching up a little, “You don’t think you would enjoy sex? Oh, buddy, you are mist-”

 

“No, Dean,” Cas interrupted. “I don’t think you understand.”

 

Dean gave him a blank look. “Enlighten me?” he offered, exasperated by the awkward angel. What do angels not like sex or something? Can they even have an orgasm? Dean shifted uncomfortably at the thought, maybe Cas  _ can’t _ have sex.

 

“Angels can copulate and climax in their vessels, Dean. That is not the problem,” Cas gave him an almost-judgmental stare. He looked very bored with this conversation.

 

Dean gave an offended look, “Get out of my head, Cas!” He never like it when the angel read his mind, it made him feel violated. He shrugged, “So what  _ is _ the problem, then?”

 

“ _ Women _ Dean,” Cas’ hands rested flat on the table. His face scrunched uncomfortably, “I don’t enjoy the company of  _ women _ .”

 

Dean’s eyes widened and he sat back in the booth with a wide grin. Cas was looking at into his lap, his ears red with embarrassment, “Dude, chill. I’m not- uh. I’m not judging you. Just a little surprised, that’s all. An angel of the lord is the last person I would expect to, uh, well to like dick.”

 

Cas’ face was now very red, but Dean was just smiling.

 

“Well this was my bad then,” Dean said, an amused look on his face as he gestured to the room around him. And on to plan B, “Come with me, I have another idea. And I know you’re gonna like this one.”

 

“Dean…” Cas said tiredly.

 

“No, seriously. Just come with me. It’ll be worth it, I promise,” he said with a wink. Cas couldn’t resist following the hunter. He had nothing better to do tonight than be embarrassed countless times by Dean.

 

They walked out of the building, and Dean climbed into the Impala, Cas sluggishly following. 

“Where are we going?” he asked, a note of uneasiness in his voice.

 

“Just wait and see, Cas.”

 

It only took about fifteen minutes in the car before Dean pulled into a parking lot. Cas recognized the lit up sign, they were at a motel. Now he was confused.

 

“Dean, I am not sure I understand your intentions. Why are we at a motel?” he asked, he was confused but he trusted the hunter to not put him in a bad place. Though he couldn’t imagine what the hunter had in mind, they had already ruled out hookers earlier. No matter how curious, he still respected the Dean’s earlier wishes, he didn’t pry into the hunter’s mind to see what he had in store.

 

“Well, I’m gonna go get us a room. You stay here,” he said to the angel. “I’m not subjecting another motel keep to your terrible social abilities if I don’t have to.” Cas’ eyes squinted as he looked at Dean, “Don’t get so defensive. Didn’t I say you were gonna like my plans?”

 

Cas rolled his eyes and sat back in the passenger side seat, crossing his arms as he waited for Dean to get out of the car. Dean Winchester was a confusing human being, and cocky, Cas’ mind supplied. 

 

The hunter left the car with a victorious smile on his face and walked down the pavement to the front entrance. It took all of five minutes for him to get a key, coming back with the same grin as before. Cas huffed in annoyance.  _ Hunters. _ Always so full of themselves. Though he couldn’t deny that he liked to spend time with them, Dean in particular. There was just something about the hunter that Cas was drawn to, maybe it was because they had been through so much together or maybe it was because he pulled Dean out of hell but he found himself infatuated with the human. 

 

Dean jingled the keys at him, waving at him to get out of the car. The angel followed Dean down to room ten, where he opened the door and walked in as if it had been his own home. The room was a dark red and the tan carpets were stained in a couple places, but it was overall a decent room. In the middle of the room was one full sized bed, which Cas thought was rather peculiar because he had never seen Dean order a room with only one bed before. He shrugged it off, though, the hunter probably took into account that the angel didn’t sleep.

 

Dean looked at him, his face transforming from a smug grin to an almost self-conscious smile. “You’d better not tell Sammy about this,” he murmured, taking a step towards the angel.

 

“Tell Sam what-” Cas was cut off by a pair of soft, warm lips pressing against his own. He let out a surprised hiccup but didn’t pull away. His eyes were wide and he stared at the hunter in complete shock. Dean’s own eyes were closed, a look of determination on his face.

 

It was the hunter that pulled away, but Cas beat him to the first line, “Dean, I don’t understand. You like women, do you not?” And of course, Cas  _ knew _ Dean liked women. The weight of a thousand one night stands weighed on the hunter's soul, and Cas knew because he could  _ see _ it.

 

Dean’s smiled grew again into smugness, “Oh, yeah. Love ‘em. Men too.” Dean smiled like it was the most casual thing he could say, but his heart was thudding in his chest. He hadn’t told anyone  _ ever _ , not even Sam, though he could guess the kid had some suspicions. “It’s called  _ bisexuality _ ,” he said sarcastically.

 

Cas rolled his eyes for the hundredth time that night, “I’m aware of what it is called, Dean. I was just not expecting it from you. Is Sam aware?”

 

Dean’s posture straightened, “No, and you’re not gonna tell him. Who I screw is none of his business.”

 

Cas’ eyebrows furrowed in concern, “Do you think Sam would not accept you? Because I believe he is a fairly open-minded person, I do not expect-”

 

“No, no, Sam would be fine with it. He’s all liberal like that anyways, especially after college. No, I just- I like my closet, it’s safe in here. Ya Know?” Dean explained. This was not going according to plan. He expected to fuck Cas, have a great night, and go nab Raphael in the morning. Not this heart-on-heart coming out to each other crap.

 

“Dean, I can assure you we are  _ not _ in a closet,” Cas said, confused.

 

Now it was Dean’s turn to roll his eyes, “No, Cas, it’s a figure of speech, like, uh- you know what? Don’t worry about it.”

 

They stared at each other awkwardly for a moment, before Dean couldn’t stand it anymore, “So do you want to fuck me or what?” He hoped he wasn’t misreading the situation, or misreading Cas. The angel had a preference for him, he noticed that in the past couple of years. He could be wrong, of course. Maybe Cas wasn’t into him.

 

“Dean, you shouldn’t have to feel obligated to do this,” Cas sighed. 

 

Dean was quick to correct him, “No, no, I don’t feel obligated, Cas. Believe me, if I didn’t want to do it, I wouldn’t. But you’re hot Cas, I mean your vessel is at least. And I like you Cas, you’re a good guy,” Dean said, the light tone of self-consciousness in his voice. “Look while you were getting laid, I was gonna go and get some myself, alright? So it’s not like I had other plans… and it’s been a while since I’ve been with a guy,” Dean rubbed the back of his neck awkwardly. “Thing is, do you want to fuck me? Because, I mean, I get it if you don’t. No hard feelings or anything, I just thought I’d off-”

 

Cas pulled Dean in for a kiss, much to the hunter’s surprise. He welcomed it though, fingers lacing into Castiel’s unruly mess of hair as he lead the angel through it. There was much to learn, but Cas was doing well so far, if not a little excited.

 

He pulled back for a second, “Slow,” he warned, leaning back in and taking Cas’s lips in his own. His hand returned to Cas’ hair, and soon they were forming a rhythm, bodies moving in tandem. It was getting rougher and faster and Dean was starting to lose control as Cas took over. The sounds of panting and groaning, teeth clashing together, and the small whines Dean was trying so desperately to cover up were filling the air. 

 

It had been so long since someone took control like this, most of the time he only ended up with women because Sam was around and when he could snag himself a guy, they usually, unfortunately, wanted to be manhandled as much as he did. He always gave in a took the dominant role, which always ended in him fucking the guy instead of vice-versa. Maybe it was because he was a nice guy, or maybe because he didn’t like feeling vulnerable all that often and bottoming was practically the definition of it. The entire situation revolves around a man fucking him in the ass for Christ’s sake, he couldn’t  _ not _ feel vulnerable. 

 

But he wasn’t worried about it now, not as Cas’ hands roamed his body, his rough fingertips sliding down his chest and around his back and grabbing his - “You wanna fuck me, Cas?”

 

Cas paused, “I thought that was the plan.”

 

Dean smirked, “That is the plan. I mean do  _ you  _ want to fuck _ me _ .”

 

Cas’ eyes lit up with understanding, “Oh, uh. If that is what you would like, Dean. I’m not sure what to do. I have no prior experience.”

 

Dean laughed, “Yeah, I know. That’s how we got into this situation, remember?” He went back to kissing the angel, distracting Cas’ nerves, “Don’t worry about it, I’ll show you what to do. First, we gotta get all these clothes off you.”

 

Dean pushed the trenchcoat off one shoulder, and then the next. Cas looked at him dead in the eyes as the coat slipped off of him and fell to the floor. Next was his suit jacket, button-up shirt, t-shirt, and - “Jesus Christ, Cas, you wear a lot of clothes. How do you not die of heat exhaustion?”

 

Cas’ eyebrows furrowed once more, “I am an angel of the lord, Dean. We are not affected by something as minuscule as a couple higher degrees in temperature.” Dean huffed and pulled the last shirt off him, smiling at his small success.

 

He had never seen Cas naked before, but he gasped a little in awe as he looked at the perfection that was Cas’ toned torso. He groaned, running one hand down Cas’ chest, hoping what was under his pants was just as pleasing. Cas was getting impatient, and he needily pulled at the hem of Dean’s shirt. He gripped the fabric, pulling it over the hunter’s head and throwing it out of the way across the room somewhere.

 

Dean smiled and pulled Cas towards him, groaning as their chests touch. He kissed the angel, messy and uncoordinated and his hands dipped a bit lower to the blue-eyed man's pants. He fumbled with the zipper and unbuttoned them. In no time Dean and Cas were standing in their boxers, kissing and grabbing and grinding. 

 

Cas pushed him back against the wall, much to Dean’s surprise. Cas  _ liked _ to take control, and the hunter was in no position to stop him. He kissed Dean with a growl, his mouth moving from the hunter’s to down his neck, licking and nipping at his collarbone as Dean tried not to whine. He bucked forward, his erection grinding against Castiel’s own hardening member.

 

The hunter was brought back to his senses by Cas’ rough voice, “Despite my actions just now, I’m not actually sure what I should be doing next.”

 

Dean barked out a laugh, pushing the angel off him. His fingers dipped below the waistband of his boxers, and he slipped them off, revealing his hard erection. Cas looked down, lips opening just a little as he stared at Dean’s cock. When he looked back into Dean’s eyes he looked completely fucked out, apparently, the show was all the angel could take before he was dragging his boxers down and off him and practically throwing Dean onto the bed.

 

“Need lube,” Dean huffed as Cas attacked him with his lips. The angel seemed to be everywhere, lips littering all over his mouth and neck and chest, hands roamed and gripping his skin. Dean felt something manifest in his hand and he smiled as he looked down at the small bottle of KY he was holding, “Nifty trick there, Cas.”

 

He rolled the angel over onto his back and climbed on top of him. Cas looked impatient and angry that Dean had broken the kiss, but he waited. Dean opened the bottle of lube and poured a fair amount on his fingertips, reaching behind him with a sigh as they brushed across his hole. He started to kiss Cas again, this time it wasn’t so desperate, it was slow and patient as Dean slowly worked one finger into his waiting entrance.

 

He groaned at the feel of it. It had been awhile since he got fucked, yes, but it had been even longer since he fingered himself. He forgot how it felt, to have his fingers moving around inside of him. He forgot about the delectable burning sensation or the fullness he felt. It wasn’t long before he had a whole finger up his ass, his pointer finger sliding in and out of him with ease. 

 

Cas seemed distracted as he was kissing Dean, moving his head erratically as he tried to get a good look at what was going on. “You wanna finger me, Cas?” Dean asked as he ground down onto the angel, their cocks sliding past each other with a delicious friction.

 

Cas groaned, “Yes, Dean.” Dean’s hand moved from Cas’ chest to his hand, and he lead the angel's fingers to his mouth. He swallowed them down, licking and sucking and making them wet. And then he released Cas’ thick fingers from his mouth and pulled them down to his ass. His own finger slipped out of his entrance, so Cas’ fingers could replace them. All the while their eye contact remained. 

 

Dean had always fucked people with a certain complete lack of emotion. He had fun, and then he left. That was his way, that was the way of the job. But this… he wasn’t sure what to make of this. With Cas’ eyes drilling into his soul, and the overwhelming shocks everywhere the angel touched.

 

Dean’s mouth hung open as two thick fingers entered him slowly. He groaned, eyes closing and grip tightening on Cas’ chest as the angel thrusted into him, “ _ Fuck _ …” he whispered.

 

Cas started to scissor him open, and Dean was losing his grip, letting out little  _ ah ah ahs _ everytime Cas thrusted up. He pushed down onto the angel’s fingers with a low groan. He could feel the pads of his fingertips brush by that sweet spot every couple thrusts, almost touching it but not quite. He was leaning back, he only had to move just a little closer and… “Cas! Oh,  _ fuck _ .” Currents of pleasure rolled through his body.

 

Cas was almost startled, did he hurt the hunter? No, that was a moan of delight, it had to be.

 

“Good, that was good,” Dean reassured him. “Prostate,” is all he said. Cas nodded, slightly familiar with what he was talking about, and continued, trying to aim for that spot again.

 

And he did, over and over and over with an aggression that had tears prickling in his eyes. Dean didn’t think Cas understood what the word overwhelming meant, and obviously had no realistic boundaries when it came to what his partner could take. But he liked it, the overstimulation, his cock so hard it was painful, and three long and thick fingers ramming into him, stopping every thrust or so to circle his prostate. He was letting out loud whimpers, his nails digging into Cas’ shoulder. “Cas, Cas. ‘m ready, I’m  _ ready _ .” The angel's fingers slowed and Dean wasn’t sure if he was relieved or sad.

 

“Condom?” Cas asked, wiping the tears from Dean’s eyes. Dean almost laughed at the angel’s bluntness. He could barely breathe after the finger-fucking Cas gave him and he couldn’t believe the angel had the audacity to just flat out ask him a question like that with such innocence and reverence like he wasn’t just ramming his fingers up another man’s ass.

 

“Don’t worry about it. I’m clean, you’re an angel of the lord. We’ll be fine,” he says with an exhausted smile. “You’re on top though,” he says as he rolls over onto his back.

 

The angel seems happy with this change, eagerly getting to his knees in front of the hunter. He looks down at the hunter, an unreadable expression on his face, “Do you believe this lubricant should suffice or should I add more?”

 

Dean laughed, and Cas gave him a weird look, “Why are you laughing? It was a reasonable question.”

 

Dean nodded, he cleared his throat and stopped laughing, still with an amused look on his face, “Just fuck me, Cas. Go slow.”

 

Cas nods, and Dean feels the blunt press of the head of his cock pressing inside of him. He gasps at the intrusion, his heads pressing back into the pillow as he lets out a small moan. Cas grips Dean’s hips in effort as he slowly sheaths himself inside the hunter. When he bottoms out, both of them moaned in unison. 

 

He tilts Dean’s head up, the hunter practically panting, and he kisses him. This was by far the most confident virgin he had ever slept with. And he felt good, hot and thick inside him, leaving a delightful burn. After a minute he pulled back. “Cas, move,” he pleaded. 

 

Cas gave him one last kiss and then got to his knees once more. He looked down at his Dean’s hole, with his cock stuffed deep inside, and he pulled out. Dean’s hips bucked involuntarily at the movement inside of him, and Cas thrusted back, his balls slapping against the hunter’s ass.

 

“ _ Yes _ ,” Dean hissed as the angel’s cock slid right past his prostate. Cas thrusted again, harder this time. Dean grabbed his bicep and throws his head back with a moan. Cas groaned, and smiled. This felt good,  _ very _ good, and he knew now why the humans loved it so much. Dean’s face was beautiful, all twisted in pleasure with his brows scrunched and his mouth open.

 

“You’re beautiful,” he murmured, thrusting into Dean once more, starting up a rhythm.

 

Dean’s head lifted from the pillow, “Hmm?”

 

Cas just drove his hips forward, grinding into the hunter. He was navigating his way into driving his cock straight into Dean’s sweet spot, making the hunter see stars. 

 

“Cas,  _ fuck _ . Harder, please,” Dean whined, thrusting his hips back against Castiel’s. The angel lifted Dean’s legs and grabbed him by the thighs, pulling him back on his cock. He started to drive into him harder and faster, groaning with every one of Dean’s little clenches around his cock.

 

“Fuck, please,” he didn’t know what he was asking for. All he knew was that there was a hard cock pounding inside of him, punching his prostate with every thrust. He could barely breathe, it felt so good.  _ Cas _ felt so good. He was twitching in Cas’ grip, bucking and moaning as he gripped the old, brown motel blanket beneath them, “So good,  _ so good _ .” He briefly wondered if Castiel was using his angel mojo on his or something, but that thought was knocked out of him by another hard thrust, Cas grinding into him once more.

 

And then there was a hand on Dean’s cock, and he knew it was almost over. There was no way in hell he would last much longer, not with the sweet slide of Castiel’s cock filling him up, the almost overwhelming grind on his prostate, and the firm grip on his cock, sliding up and down in tandem with his thrusts.

 

“Tell me you’re close,” he pleaded, whining as his head falls back to the pillow again. He had also never fucked a virgin who could last longer than he did.

 

Cas nodded, “Very.” He picked up the pace, chasing their climaxes. 

 

Dean was a whimpering mess, his hard and leaking in Cas’ grip. He could barely take it, he was so close,  _ so close _ , “‘m gonna come, oh  _ fuck _ .” Cas jacked him off faster, grinding his cock head into Dean’s prostate, “Oh fuck,  _ Cas _ . Cas!” Dean’s cock spurted semed across his body and Cas’ hand, and he shook in the angel’s grip. His mouth was open wide, eyes tearing up once more as his nails bit into Cas’ skin.

 

Cas smiled,  _ beautiful _ , he thought. Dean had the most beautiful soul, character, lips, mouth,  _ eyes _ . 

 

Cas continued to thrust into the hunter after the waves of bliss had ended, now slower, his eyebrows scrunched in pleasure. Dean clenched around him in encouragement, trying to catch his breath after one of the best orgasms he’s had in awhile. He let out little whines as Cas got closer and closer to the edge.

 

One thrust, two thrusts, three and… “ _ Dean! _ ” The hunter smiled at the face Cas was making, one of pure ecstasy and completion. He could feel the warm gush of come inside of him, he had never let anyone come inside him before. 

 

The angel practically collapsed on top of him, but Dean didn’t mind, he liked to cuddle (though he would never admit it). He like the pressure on top of him, it made him feel somewhat safe. Though Cas got up on his own, manifesting a washcloth into his hand. 

 

“Again with the angel mojo, I like it,” Dean gave him a wink as the angel cleaned up his torso, and around his back to his ass. “You ready to conjure up us one powerful motherfucker and find out where the hell God is?”

 

Cas gave Dean a sweet smile, “Yes, Dean.”


End file.
